To be prepared against surprise is to be trained. To be prepared for surprise is to be educated.
James Carse's perspective on the difference between training and education highlights what I think the school system should be.
Too many people complain about how their undergrad fails to prepare themselves for the job market. However, I believe the purpose of undergrad should not be training for the occupation. The proper expectation for university should be an education that makes people more resilient and adaptable to uncertainty. For job hunting, one should seek other resources, such as online courses, bootcamp or self-learning, that aim to train for specific skills.
In other words, training makes the future less uncertain, while education makes the future less confined. In James Carse's more poetic words:
"Education discovers an increasing richness in the past, because it sees what is unfinished there. Training regards the past as finished and the future as to be finished. Education leads toward a continuing self-discovery; training leads toward a final self-definition. Training repeats a completed past in the future. Education continues an unfinished past into the future."
This view is also quite similar to what Kevin Kelly mentioned in his 103 Bits of Advice I Wish I Had Known:
Rather than steering your life to avoid surprises, aim directly for them.
Don't keep making the same mistakes; try to make new mistakes.